Sturgill Simpson Essentials

In a way, Sturgill Simpson is the ultimate outlaw country artist. While his dusty baritone and hard-bitten twang hark back to the heyday of old-school outlaw Waylon Jennings, he doesn't stop there. Few other artists of his ilk can cover ‘90s grunge tunes and ‘80s synth-pop hits, sing about spacemen and philosophy, and slip straight-up soul arrangements onto their records without sacrificing a single ounce of hard-country cred. The Kentucky boy is too weird for Nashville and too country to be alt-country—and that's just the way he likes it.